137848-28-3

Basic information

• Product Name: (R)-NOBIN
• Synonyms: S-(-)-2-AMINO-2'-HYDROXY-1,1'-BINAPHTYL;(S)-(-)-2-AMINO-2'-HYDROXY-1,2'-BINAPHTHYL;(R)-(+)-NOBIN;R-NOBIN;R-(+)-2-AMINO-2'-HYDROXY-1,1'-BINAPHTYL;(R)-(+)-2-AMINO-2'-HYDROXY-1,1'-BINAPHTHYL;R-2'-AMINO-1,1'-BINAPHTHALEN-2-OL;(R)-(+)-2-AMINO-2'-HYDROXY-1 1'-BINAPHT
• CAS NO: 137848-28-3
• Molecular Formula: C₂₀H₁₅NO
• Molecular Weight: 285.34
• Product Categories: chiral;CHIRAL COMPOUNDS;Chiral Compound;Auxiliaries,Catalysts
• Mol File: 137848-28-3.mol
• Article Data: 32

Chemical Properties

• Melting Point: 171.0 to 175.0 °C
• Boiling Point: 471.5 ºC at 760 mmHg
• Appearance: /
• Density: 1.275 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.90±0.50(Predicted)
• CAS DataBase Reference: (R)-NOBIN(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-NOBIN(137848-28-3)
• EPA Substance Registry System: (R)-NOBIN(137848-28-3)

Safety Data

• Hazard Codes: Xi,N
• Statements: 41-50/53
• Safety Statements: 26-39-60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 137848-28-3(Hazardous Substances Data)

Usage

Chemical Properties

Red crystal

Uses

(R)-(+)-2′-Amino-1,1′-binaphthalen-2-ol may be used as a catalyst in the asymmetric PTC (phase-transfer catalysis) synthesis of α-amino acids. (R)-NOBIN reacts with trans-azobenzene-4,4′-dicarbonyl chloride to form poly(ester-amide)s, which shows backbone light-regulated chiroptical response.

General Description

(R)-(+)-2′-Amino-1,1′-binaphthalen-2-ol is a non-symmetrically substituted 1,1′-binaphthalene ligand.

Upstream product

• 91-59-8 naphthalen-2-ylamine 
• 135-19-3 β-naphthol 
• 602-09-5 1,1'-bi-2-naphthol 
• 74974-14-4 2,2’-bis(diphenylphosphinoamino)-1,1’-binaphthyl 
• 194-63-8 dinaphtho[2,1-b;1',2'-d]furan 
• 2449-05-0 dibenzyl azodicarboxylate 
• 134532-03-9 2-amino-2’-hydroxy-1,1’-binaphthyl 
• 32316-92-0 naphthalene-2-boronic acid 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 580-13-2 2-bromonaphthalene 
• 473699-18-2 (S)-(-)-2-(α-methylbenzylamino)naphthalene 
• 18741-85-0 (R)-1,1'-binaphthyl-2,2'-diamine 

Downstream Products

• 137848-29-4 (S)-(-)-2'-amino-[1,1'-binaphthalene]-2-ol 
• 194-59-2 7H-dibenzo[c,g]carbazole 

Relevant articles and documents

Tandem approach to NOBIN analogues from arylhydroxylamines and diaryliodonium salts: via [3,3]-sigmatropic rearrangement

Herein, we present a transition-metal free direct O-arylation of arylhydroxylamines employing diaryliodonium salts as arylation reagents to form transient N,O-diarylhydroxylamines that could subsequently undergo [3,3]-sigmatropic rearrangement and re-aromatization to afford structurally diverse NOBIN analogs in good to excellent yields under mild conditions.

Synthesis and resolution of racemic 2-amino-2′-hydroxy-1,1′-binaphthyl

The title compound 3 has been prepared via a highly selective, Cu(II)-mediated cross-coupling of 2-aminonaphthalene 1 and 2-naphthol 2 and resolved into enantiomers via crystallization of diastereoisomeric salts with (1S)-(+)-10-camphorsulfonic acid. The method has been optimized and the use of chromatography eliminated.

Synthesis of Enantiomerically Pure 2,2'-Dihydroxy-1,1'-binaphthyl, 2,2'-Diamino-1,1'-binaphthyl, and 2-Amino-2'-hydroxy-1,1'-binaphthyl. Comparison of Processes Operating as Diastereoselective Crystallization and as Second-Order Asymmetric Transformation

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Kinetic resolution of axially chiral 2-amino-1,1′-biaryls by phase-transfer-catalyzed N-allylation

Going through a phase: The highly selective kinetic resolution of the title compounds, which are important chiral building blocks, was achieved by phase-transfer-catalyzed N-allylation. This synthetic method was applied to the highly enantioselective desymmetrization of a biaryl compound. Copyright

Kinetic resolution of 1,1-biaryl-2,2-diols and amino alcohols through NHC-catalyzed atroposelective acylation

We present here a highly efficient NHC-catalyzed kinetic resolution of a wide range of 1,1-biaryl-2,2-diols and amino alcohols to provide them in uniformly ≥99% ee. This represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found to have a significant effect on the enantioselectivity of the process.

A Chiral Iron Disulfonate Catalyst for the Enantioselective Synthesis of 2-Amino-2′-hydroxy-1,1′-binaphthyls (NOBINs)

A novel type of chiral redox disulfonate iron complex for asymmetric catalysis is reported. The [Fe((Ra)-BINSate)]+(BINSate = 1,1′-binaphthalene-2,2′-disulfonate) complex effectively promotes the enantioselective oxidative cross-coupling between 2-naphthols (1) and 2-aminonaphthalene derivatives (2), affording optically enriched (Ra)-2-amino-2′-hydroxy-1,1′-binaphthyls (NOBINs) with exceptional yields and enantioselective ratios (up to 99% yield and 96:4 er). The [Fe((Ra)-BINSate)]+catalyst was designed as a chiral version of FeCl3with multicoordination sites available for binding the two coupling partners 1 and 2 as well as the oxidant. Our structure-selectivity and activity study, which covered most of the important positions in the NOBIN scaffold, revealed the effect of different substitution patterns on the coupling efficiency and stereoselectivity.

Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction

A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.